The James Altucher Show

A Note from JamesI’m honored to have today’s guest: Tristan de Montebello, a finalist in the World Championship of Public Speaking. He also co-founded UltraSpeaking (ultraspeaking.com/james), where he teaches techniques to improve communication through games and real-world practice. We even played some of those games during this episode, and they surprised me with how much they revealed about my own speaking.Public speaking isn’t just about giving a good talk—it’s about understanding who you are, what you stand for, and how you connect with others. I’ve been speaking for more than 25 years, but I’m still always looking for ways to improve. At the end of the day, sharing ideas—through writing, storytelling, or speaking—is how you can change the world.This conversation with Tristan is fascinating because he’s gone from zero experience to becoming one of the best in the world, all while reverse-engineering what it takes to truly connect with an audience.Episode DescriptionHow does someone go from a complete beginner to a world-class speaker in less than a year? Tristan de Montebello did exactly that—and in the process, he uncovered the strategies, mindsets, and training methods that make communication powerful.In this episode, James and Tristan break down the mechanics of storytelling, humor, vulnerability, and flow in speaking. They explore why audiences respond the way they do, how to use analogies to create connection, and why mindset is the foundation of every great communicator. Whether you’re on a stage, in a meeting, or simply trying to share an idea with friends, these lessons will change the way you approach communication.What You’ll LearnHow Tristan went from novice to World Championship finalist in under a year.Why humor and vulnerability are essential ingredients for authentic connection.Practical ways to use storytelling and analogies to make ideas stick.How to handle insecurity, fumbles, and “tough audiences” without breaking flow.Why mindset—not technique—is the foundation of great communication.Timestamped Chapters[01:00] A Note from James and introducing Tristan de Montebello[04:15] Inside the World Championship of Public Speaking[07:45] Humor, storytelling, and why connection matters[11:10] The Fear Olympics: lessons from Tristan’s grandmother[16:30] “Never be the hero of your own story”[20:15] Breaking down stories like Finding Nemo[24:45] How Tristan trained humor like a stand-up comic[28:30] What great speakers and clowns have in common [33:20] Managing insecurities and staying in character[41:40] From finalist to struggling in an online mastermind[50:20] Slacklining as a metaphor for learning[54:10] Building analogies as a core communication skill [60:30] Reading tough or quiet audiences[67:15] Handling bias and building trust with skeptical crowds[69:45] Flow state in public speakingAdditional ResourcesUltraSpeaking – ultraspeaking.com/jamesToastmasters International – toastmasters.orgRich Dad Poor Dad by Robert Kiyosaki – Amazon linkEight Mile (film referenced by James & Tristan) – IMDbSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from JamesWhat does it take to make a discovery that changes the world? Think about landing on the moon — a true moonshot. Along the way, countless technologies were invented that reshaped life back on Earth.My guest today, Astro Teller, has been part of that same kind of world-changing work. At X — Alphabet’s Moonshot Factory — he’s led projects that gave us self-driving cars, Google Brain, drone delivery, augmented reality with Google Glass, and much more. We even talk about quantum computing, drones that bring your groceries to your backyard, and the mindset it takes to believe in something that once sounded like science fiction.Astro and I first crossed paths when I visited Google X back in 2012 or 2013. He was on this podcast in 2015, and now, ten years later, he’s back to talk about his own show — The Moonshot Podcast — and the latest bold projects that could shape our future.Episode DescriptionAstro Teller, Captain of Moonshots at Alphabet’s X, joins James to share how impossible-sounding ideas become real. From Waymo’s self-driving cars to Wing’s drones, from the birth of Google Brain to breakthroughs in quantum networking and modernizing electric grids, Astro explains the engineering mindset that drives innovation.This episode goes beyond technology — it’s about how to think like a moonshot maker. You’ll hear how X chooses projects, why systems engineering often matters more than pure science, and how to break down massive problems into solvable steps.What You’ll LearnThe three elements that define a true moonshot at X.Why self-driving cars succeeded not because of new science, but because of paradigm-shifting systems engineering.How Google Brain kickstarted the modern AI revolution by betting on scale when neural nets were out of fashion.Why Wing’s drone delivery service may soon feel as ordinary as rideshare apps.How Project Tapestry is mapping and optimizing the electric grid to cut connection times from years to days.The promise (and risks) of quantum networking, quantum sensing, and the looming “Q-Day” when current cryptography could break.Why empathy is crucial for workers displaced by new technologies.Timestamped Chapters[01:00] A Note from James[04:00] Inside Alphabet’s Moonshot Factory (X)[06:00] Defining moonshots: problem, radical solution, breakthrough tech[08:00] Waymo and the hidden challenges of self-driving cars[13:00] Safety, comfort, and the “body language” of cars[17:00] Google Brain and the rebirth of neural networks[20:00] Cats, YouTube, and AI’s first big proof point[23:00] Wing: drones delivering groceries like magic[29:00] Moonshot mindset vs. the Apollo mission[31:00] How X evaluates and selects moonshots[34:00] Breakthroughs behind Waymo and simulation at scale[39:00] What if every car was autonomous?[40:00] Project Tapestry: modernizing the electric grid[45:00] Mapping PJM and national-scale grids[46:00] Lessons from Google Glass: too early, or misframed?[48:00] The future of AR glasses and AI assistants[51:00] Why X left longevity research to Calico and Verily[52:00] Quantum computing, networking, and sensing explained[57:00] The coming “Q-Day” and what it means for security[59:00] AI, jobs, and the importance of empathy[61:00] Closing thoughts and Astro’s Moonshot PodcastAdditional ResourcesThe Moonshot Podcast with Astro Teller (YouTube)X, the Moonshot FactoryWaymo (Self-Driving Cars)Wing (Drone Delivery)Google BrainProject Tapestry – Grid ModernizationPJM Interconnection (Eastern US Grid)Calico (Alphabet’s Longevity Research)Verily Life SciencesSandbox AQ (Quantum & AI)Carnegie Mellon University School of Computer ScienceSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from JamesThere’s always been debate about whether college is worth it. But what if there’s a better alternative—one that actually prepares you to become the person you want to be? My good friend Matt Smith just wrote a book with Doug Casey called The Preparation. It’s not theory—he’s been putting his own son through it as a real-world experiment. Instead of college, Maxim has spent the past two years learning skills like EMT training, firefighting, building houses, working cattle, and even launching a business. This is a practical roadmap for turning those years of 18–22 into a hero’s journey. I loved this conversation, and I’m sending the book to all of my kids.Episode DescriptionJames talks with entrepreneur and writer Matt Smith about his new book The Preparation, co-authored with Doug Casey. The book lays out a four-year alternative to college built around “cycles”—three-month intensive experiences designed to build practical skills, personal codes, and real-world wisdom. From earning an EMT license to fighting wildfires, training in Muay Thai, or running a small business, these cycles are designed to help young people become independent, capable, and resilient. James and Matt discuss why the traditional college path often fails, how to build a personal code of values, and why the future belongs to “expert generalists” who know how to learn across disciplines.What You’ll LearnWhy “be, do, have” is a more powerful framework for life than chasing possessions or credentials.How creating a personal code builds self-respect and identity.Why intergenerational relationships matter more than peer validation.How cycles of hands-on learning—from EMT work to entrepreneurship—prepare young people better than a classroom ever could.Why becoming an expert generalist is the best hedge against a future dominated by AI and automation.Timestamped Chapters[00:00] A Note from James: College vs. alternatives[01:00] Introducing Matt Smith and The Preparation[03:00] Origins of the book and Doug Casey’s vision[05:00] Writing the book for his son Maxim[06:00] Why homeschooling replaced high school[07:00] “Be, Do, Have” explained[09:00] Stacking cycles vs. stacking skills[10:00] Why the book focuses on young men (and how women can adapt it)[11:00] How to build your own cycle[13:00] Why traditional education fails to prepare people for real skills[14:00] Establishing a personal code[16:00] Examples of personal rules for self-respect[18:00] Practicing courage and choosing virtues[20:00] Skills Maxim has gained so far—EMT, chess, horses, firefighting[22:00] Adventures with Doug Casey and small-country nation building[24:00] Maxim’s cycles: EMT work, ranch apprenticeship, wildfire EMT[27:00] Structure, resistance, and learning by doing[28:00] Shelter Institute and learning to build a house[29:00] Entrepreneurship cycle: precision agriculture with drones[31:00] Lessons from entrepreneurship[32:00] Muay Thai training in Thailand[33:00] Cooking school in Florence[34:00] Travel with purpose vs. aimless wandering[36:00] James on biographies and meaningful decisions[37:00] Preparing for AI and the future of work[39:00] Why being an “expert generalist” matters[41:00] Learning how to learn across environments[42:00] The problem with peer-only education[44:00] Intergenerational relationships as mentorship[45:00] What comes after the preparation[47:00] Why the program can work for adults too[49:00] Rethinking retirement as another cycle of preparation[56:00] Matt’s personal growth through writing and learning new skills[58:00] Designing The Preparation as a beautiful, interactive book[59:00] Closing thoughts and sending the book to the next generationAdditional ResourcesMatt Smith & Doug Casey — The PreparationDoug Casey’s Take (Podcast): YouTube ChannelDoug Casey’s Official Site: internationalman.comThe Shelter Institute (Learn to Build a House): shelterinstitute.comMuay Thai Training in Thailand (Example School): Santai Muay Thai GymFlorence Cooking School Example: Apicius International School of HospitalityStripe Press (Books mentioned by Matt): stripe.pressDoug Casey’s Classic Book — Crisis Investing: AmazonSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode DescriptionJames sits down with Case Kenny, author of The Opposite of Settling and host of New Mindset, Who Dis?, to talk about how our expectations around relationships shape the way we date and commit. Case shares the research, stories, and mindset shifts that helped him go from avoiding commitment in his twenties to finding fulfillment in a relationship that amplifies his independence. This episode challenges old narratives about “settling down” and offers a practical framework for building relationships that energize rather than diminish.What You’ll LearnWhy “settling down” is the wrong framework for love—and how to reframe it as “settling up.”How the liking gap skews our perception of how others see us, and what that means for dating.The importance of dating to be seen instead of dating to be liked.Why non-conforming traits (your “weirdness”) can actually make you more attractive.How playfulness and humor serve as the foundation for strong, lasting relationships.Timestamped Chapters[00:00] Rethinking independence in relationships[01:00] James introduces Case Kenny and The Opposite of Settling[02:00] Why the phrase “settle down” shaped Case’s early resistance to commitment[05:00] Letting relationships fade: what Case learned from avoidance[07:00] Meeting Emily and the power of a “slow burn”[09:00] Timing vs. compatibility in finding a partner[11:00] The “liking gap” and how it affects dating behavior[13:00] Performance mode vs. being present[14:00] Dating to be seen, not just to be liked[15:00] The value of non-conforming traits in attraction[17:00] From introversion to self-expression through podcasting[20:00] Knowing yourself before you can know what you want[21:00] The peak-end rule and distorted memories of relationships[23:00] Appreciating past relationships without villainizing them[25:00] How the brain can reinforce unhelpful dating patterns[27:00] The case for showing up fully on first dates[29:00] Learning from rejection and getting clarity fast[31:00] Why regret often comes from the wrong relationship, not from being single[33:00] Playfulness as the true purpose of relationships[35:00] Humor and “bids for connection” as relationship foundations[37:00] The importance of noticing your partner[38:00] Why James listened to standup comedy before dates[39:00] Wrapping up with Case KennyAdditional ResourcesCase Kenny — The Opposite of Settling: PenguinRandomhouse.comCase Kenny — Single Is Your Superpower: New Mindset, Who Dis?New Mindset, Who Dis? (Apple Podcasts): Apple PodcastsThe Gottman Institute — “Bids for Connection” (overview): Start paying more attention to bids. Gottman InstituteResearch — “The Liking Gap” (Boothby et al., 2018, PDF): Yale Clark Relationship Lab. Clark Relationship LabExplainer — Peak–End Rule: The Decision LabCase Kenny on X (Twitter): @thecasekennySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode Description:Hosted by James Altucher (serial entrepreneur, bestselling author of "Choose Yourself," podcaster, hedge fund manager, chess master, and investor in over 20 companies, with expertise in crypto and AI) and Joseph Jacks (founder and general partner of OSS Capital, the world's first VC firm dedicated to commercial open-source software; early-stage investor in AI and open-source tech, previously Entrepreneur-in-Residence at Quantum Corporation).In the premiere episode, James and Joe explore Bittensor's decentralized AI ecosystem, contrasting it with centralized giants like xAI's Grok 4. They discuss subnets providing GPUs, datasets, and models; proof-of-useful-work mining; building custom AI agents; and Bittensor's potential to outpace Big Tech in achieving superintelligence.Plus, tokenomics, real-world apps, capitalism parallels, and bold predictions on TAO's future value.Key Timestamps & Topics:00:00:00 - Intro: Podcast overview, AI/crypto news (Grok 4, Bitcoin ATH), centralized vs. decentralized AI.00:09:00 - Proof of Useful Work: Mining datasets, models, inference on Bittensor.00:10:00 - Subnet Deep Dives: Dataverse (13) for data scraping; building trading models.00:16:00 - Chutes (64): Cheap AI inference, e.g., Bible chatbot at 1/50th OpenAI cost.00:23:00 - Agentic AI: Building owned agents, avoiding Big Tech biases/control.00:28:00 - Scaling & Future: Decentralization's infinite potential; Bitcoin compute parallels.00:33:00 - Superintelligence Path: Bittensor faster than Elon; energy/chip challenges.00:34:00 - Bittensor's Early Stage: Like 1990s internet, needs better user interfaces.00:38:00 - Chutes Economics: 10T+ tokens served, 4.4K H100 GPUs, user growth.00:50:00 - Valuation & Growth: Subnets as companies; TAO potentially 5-10x Bitcoin.01:02:00 - Bittensor as Pure Capitalism: Incentives for supply/demand; upgrading equity models.01:09:00 - Centralization Risks: Elon/Meta control; Bittensor's global solution.01:13:00 - Wrap-Up: Teasing future episodes on subnets, AI ventures.Key Takeaways:Bittensor incentivizes ~20-100K GPUs permissionlessly, rivaling xAI at zero CapEx.Subnets like Chutes (inference) and Dataverse (data) enable cheap, owned AI models for anyone.Decentralization democratizes AI talent/compute, potentially building AGI faster than centralized efforts.Quote: "Bittensor is the most expressive language of value in the history of languages of value." – Joseph JacksResources & Links:Bittensor Official: bittensor.comTaostats (Explorer/TAO App): taostats.ioSubnet 64 (Chutes): taostats.io/subnets/64Subnet 13 (Dataverse): macrocosmos.ai/sn13Akash Network: akash.networkxAI: x.aiFollow Hosts: @jaltucher & @josephjacks_ on XSubscribe for more on Bittensor subnets, AI building, and crypto trends! Leave a review and share your thoughts. #TheTaoPod #Bittensor #DecentralizedAI #TAOToday's Advertisers:Secure your online data TODAY by visiting ExpressVPN.com/ALTUCHERElevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audience.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:"Anatomy of a Con Artist. The 14 red flags to spot scammers, grifters, and thieves". This is a book—an amazing book—by Johnathan Walton.Check out his podcast Queen of the Con, and his new one Cocaine Air. We talk about both in this episode. But his book, Anatomy of a Con Artist, is just dead on.Johnathan shares how he got conned out of nearly $100,000 by someone posing as an Irish heiress. He breaks down not only that story but others—showing how all these professional con artists use the same tricks. The red flags are universal.And honestly, I’ve felt conned before. Reading this book really opened my eyes. The stories are incredible, and Johnathan’s a fantastic storyteller. You’ll hear it for yourself.Episode Description:James talks with Johnathan Walton—TV producer turned con artist hunter—about the psychology, tactics, and red flags of professional scammers. After being conned out of nearly $100,000 by someone posing as an Irish heiress, Walton went public, brought his scammer to justice, and began investigating other cases.Together, they unpack how emotion—not intellect—is the con artist’s favorite tool, and how even smart, skeptical people can be taken in. Walton explains the 14 red flags every scammer throws up, why victims rarely report what happened, and how shame and silence help cons thrive.Plus: the untold story of Walton’s family losing millions to a Jamaican Ponzi scheme, how Satanists helped him track a fugitive scammer, and why AI will never replace the twisted brilliance of the human con.What You’ll Learn:How professional con artists emotionally manipulate even intelligent peopleThe 14 red flags common to nearly every scamWhy victims often stay silent—and how scammers exploit shameHow “beak-wetting” creates false trust in investment scamsWhy AI can't replicate the improvisational storytelling of real-world con artistsTimestamped Chapters:[00:00] A con artist doesn't outsmart you—they outfeel you[01:00] James introduces Johnathan Walton and his work[02:00] Behind the HBO show “Wahl Street” and producing during COVID[04:00] AI in storytelling: potential and limitations[07:00] Johnathan’s $100K con: the fake Irish heiress and inheritance scam[10:00] Red Flag: TMI—“too much information” and the psychology behind it[14:00] The trap of emotional vulnerability[17:00] How scammers build false intimacy[20:00] Johnathan’s early career and his resilience to shame[24:00] How she drained him slowly: death by a thousand cuts[25:00] The first lie that blew everything open[28:00] Uncovering her global scams and getting her arrested[30:00] Scamming Satanists and extradition to Northern Ireland[32:00] Psychopathy vs. regular criminals: how con artists differ[34:00] Why she targeted him: the do-gooder trap[36:00] Breaking down the red flags from his book[41:00] Ponzi schemes and beak-wetting in his own family[47:00] Wealthy victims who never go public[49:00] The story of NFL QB Eric Kramer and the con-woman wife[52:00] Talking victims out of suicide[53:00] Johnathan’s own mother was conned—by a family friend[55:00] The isolation technique and divide-and-conquer[57:00] How to protect yourself: background checks and gut checks[59:00] Spotting con artists in real life[01:01:00] Cocktail party con: the OnlyFans couple from Arizona[01:02:00] Final thoughts and how to follow Johnathan’s workAdditional Resources with Working Links:Book: Anatomy of a Con Artist by Johnathan Walton Available on Apple Books: Anatomy of a Con Artist Also listed on Penguin Random House: Anatomy of a Con ArtistPodcast: Queen of the Con by Johnathan Walton On Apple Podcasts: Queen of the Con (Apple Podcasts)Podcast: Cocaine Air by Johnathan Walton On Apple Podcasts: Cocaine Air (Apple Podcasts)Movie: Sharper (Neo-noir thriller) streaming on Apple TV+ Watch directly on Apple TV+: Sharper (Apple TV+) About the film and release details: Sharper (Wikipedia page)Today's Advertisers:Secure your online data TODAY by visiting ExpressVPN.com/ALTUCHERElevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audience.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:I was honored to be on the Smart Humans Podcast. I’m a big fan of the show, and I was happy they asked me on—especially since I got to talk about things I don’t usually cover here.We discussed my specific predictions for investments like Bitcoin, Ethereum, Tau, and stablecoin-related tokens like Curve and Aave. We also explored AI’s role across industries, habits that have helped me build and sell companies, and bad habits that cost me millions.This episode is packed with my thoughts on investing, crypto, AI, and the lessons from going broke—twice. I hope you enjoy this conversation as much as I did.Episode Description:In this special crossover episode, James Altucher joins Slava Rubin on the Smart Humans Podcast to talk investing, entrepreneurship, and the habits that make (and lose) fortunes. James shares his journey from early internet entrepreneur to hedge fund manager, bestselling author, and crypto investor—and the times he lost it all along the way.They dive into today’s hottest investment themes, including Bitcoin, Ethereum, Tau, stablecoins, and the intersection of crypto and AI. James also explains why he avoids bonds and real estate, the power of his “10 ideas a day” practice, and the economic trends he’s watching over the next three years.What You’ll Learn:Why James predicts Bitcoin could reach $250K by next year and $1M by 2027The case for Ethereum, Tau, Curve, and Aave in the next wave of crypto growthHow AI is transforming productivity—and why that’s bullish for the economyThe “10 ideas a day” method for rebuilding creativity and opportunityWhy avoiding certain asset classes can be as important as picking winnersTimestamped Chapters:[00:00] A Note from James: Why This Episode Is Different[02:00] James’s Journey: From Web Pioneer to Investor[06:00] Selling for $15M and Losing It All[10:00] Rebuilding Through “10 Ideas a Day”[14:00] Private Investing and Early-Stage Bets[17:00] The Crypto–Equity Crossover Trend[21:00] Why James Avoids Bonds and Real Estate[23:00] Stablecoins as the Biggest Use Case for Crypto[27:00] Picks and Shovels: Curve and Aave[31:00] Ethereum’s Potential vs. Bitcoin[34:00] Economic Outlook: AI, Productivity, and Growth[39:00] Risks, Inflation, and the Money Supply[42:00] Tau: The Decentralized AI Play[44:00] Doing > Reading for Real Expertise[46:00] Three-Year Predictions: Public and Private PicksAdditional Resources:Smart Humans Podcast with Slava Rubin: WebsiteJames Altucher on Twitter: @jaltucherChoose Yourself by James Altucher – AmazonCurve Finance (CRV) – curve.fiAave (AAVE) – aave.comEthereum (ETH) – ethereum.orgToday's Advertisers:Head to rugiet.com/JAMES and use code JAMES to get 15% off today!Secure your online data TODAY by visiting ExpressVPN.com/ALTUCHERElevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audience.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:We kept recording because the conversation wasn’t done. Part 1 was about writing and honesty. Part 2? It’s about consequences—what happens when people believe their own hype, when we confuse being loud with being right, and when storytelling gets weaponized. Ryan Holiday has written about ego, stillness, and obstacles. But this part of the conversation gets at something deeper: what happens when power and narrative collide. And how do we live with integrity when the tools we use to create can just as easily be used to manipulate?Episode Description:In Part 2 of their conversation, James Altucher and Ryan Holiday explore the darker side of influence—how public figures lose their grounding, how movements become cults, and how audience validation can steer creators away from their original purpose.They discuss RFK Jr., Jordan Peterson, and Tucker Carlson—not as political figures, but as case studies in how public personas evolve under the pressure of attention. Along the way, they wrestle with their own roles as communicators: when to speak, when to hold back, and what it really means to be useful in a world full of noise.What You’ll Learn:Why creators are vulnerable to audience captureThe line between healthy skepticism and conspiracy thinkingWhat separates honesty from manipulation in public discourseWhy power often comes at the expense of self-awarenessHow James and Ryan each wrestle with responsibility as public thinkersTimestamped Chapters:[00:00] Continuation from Part 1[01:00] How Personas Get Distorted Over Time[02:00] The RFK Jr. Conundrum[04:00] Audience Capture and Dopamine Loops[06:00] When Truth Becomes Optional[08:00] Jordan Peterson and the Burden of Symbolism[10:00] Platform Power vs. Message Integrity[11:00] What Happens When You Start Believing Your Own Brand[12:00] The "Edge" as a Career Strategy[13:00] The Slippery Slope from Insight to Grift[15:00] Building a Philosophy Business[16:00] How Stoicism Can Be Used or Abused[17:00] Tucker Carlson, Outrage, and Narrative Control[19:00] Being Useful vs. Being Loud[21:00] When You’re More Known Than You Are Understood[23:00] The Fear of Changing Your Mind[24:00] When Silence is the Most Ethical Choice[25:00] Creating in Public Without Losing Yourself[27:00] The Most Powerful Words: “I Don’t Know”Additional Resources:Ryan Holiday’s website: ryanholiday.netEgo Is the Enemy by Ryan Holiday: AmazonJames Altucher on Twitter: @jaltucherThe Daily Stoic podcast: Daily StoicSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:Ryan Holiday is one of the few writers I consider a peer—not just because of the work he’s done, but because of the choices he's made along the way. We’ve both published a lot of books. We've both dealt with audiences, platforms, and the weight of having a “point of view” in a world that increasingly wants you to pick a side. This episode wasn’t meant to be a debate or an interview. It was just two people trying to make sense of the tension between creativity and truth, honesty and influence, and why sometimes the best thing you can say is nothing at all.Episode Description:In this candid and far-ranging conversation, James Altucher sits down with bestselling author Ryan Holiday to talk about the changing nature of creativity, writing, podcasting, and personal ethics in a polarized media landscape.They discuss the illusion of having to weigh in on every issue, the danger of algorithmic thinking, and how to stay true to your voice without becoming a prisoner to your audience. Whether you're a writer, a creator, or just trying to think more clearly in chaotic times, this episode offers real insight into the forces shaping our thinking—and how to resist them.What You’ll Learn:Why sharing too early can kill creative momentumHow social media shifted from expression to algorithm worshipWhy long-form podcasts might be bad for your brainHow writing differs from other art forms in its tension and permanenceThe tradeoffs between artistic freedom, platform growth, and audience expectationsTimestamped Chapters:[00:00] Writing Without Talking About It[01:00] Why Book Ideas Need Time in the Dark[02:00] Creative Compulsion vs. Discipline[03:00] Stand-Up, Dopamine, and Daily Feedback[05:00] Point of View in a Binary World[06:00] Silence, Ethics, and Speaking Up[07:00] Noise as a Form of Violence[09:00] Political vs. Philosophical Disagreements[10:00] Social Media’s Shift to Opinion Farming[11:00] The Algorithm as Audience Puppet Master[12:00] When the Audience Has You[13:00] Podcasting’s Algorithm Problem[14:00] Are Podcasts Dangerous?[16:00] Podcasting vs. Books: Tension and Craft[18:00] The Rise of the Longform Grifter[20:00] RFK Jr., Bad Ideas, and No Fact Checks[22:00] Why Audiobooks Outperform Podcasts[23:00] Can the Medium Save Us?[25:00] When Podcasts Work (And When They Don’t)[27:00] Music and the Emotional Power of Simplicity[29:00] Songs vs. Culture War Commentary[30:00] Great Lyrics, Great Feelings[32:00] Bono, Stoicism, and Making You Feel Seen[34:00] The Parasocial Magic of Fame[35:00] Acting, Politics, and Emotional Truth[37:00] Writing as the Hardest Artform[39:00] Why Great Writing Still MattersAdditional Resources:Ryan Holiday’s website: ryanholiday.netThe Daily Stoic by Ryan Holiday: AmazonJames Altucher on Twitter: @jaltucherRyan Holiday’s books on Amazon: Author PageOlivia Rodrigo – “Drivers License” (YouTube): Watch hereLed Zeppelin lyrics and discography: ledzeppelin.comU2 – “Sunday Bloody Sunday”: YouTubeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:When I first said that college was a scam, people thought I was joking—or worse. But I wasn’t. If you’re 18 and listening to this, don’t go to college. And if you’re a parent, don’t send your kid without doing the math. College doesn’t guarantee a better life anymore. In fact, it could cost you years of freedom, tens of thousands of dollars, and saddle you with debt you can’t escape. In this episode, Doug Hill and I talk about why the traditional path of “get a degree, get a job, live happily ever after” no longer holds up.Episode Description:In this second installment of the Crazy Finance series, James Altucher and Doug Hill challenge another major financial assumption: that college is necessary for success. James argues that skyrocketing tuition, guaranteed student loans, and outdated curricula make college a bad financial decision for most people. Doug, who sent four kids to college, shares his own experience and ultimately agrees—except in a few key professions.From alternative education paths to trade school opportunities, this episode breaks down the economics and psychology behind one of the most expensive decisions families ever make.What You’ll Learn:Why student loan debt is structurally predatory and practically inescapableHow government-backed loans have inflated tuition for decadesWhich professions still require college—and which don’tWhy trade schools and alternative education may offer better returnsHow personal development can happen outside the college systemTimestamped Chapters:[00:00] Don’t Go to College (Seriously)[01:00] Why “Personal Finance” Advice Feels Generic[02:00] College as a Scam, Explained[03:00] When College Is Actually Worth It[04:00] Do Doctors Really Need 8 Years of School?[06:00] The Business Degree: What Did It Even Teach?[07:00] Entrepreneurship vs. Education[08:00] The Myth of Higher Earnings[09:00] Remedial Programming After Grad School[10:00] Why Tuition Keeps Rising[11:00] Government Guarantees = No Risk for Colleges[12:00] The Hidden Costs and Opportunity Costs[13:00] Who Actually Benefits From College?[14:00] Trade Schools and Skilled Labor[15:00] Electricians, Mechanics, and the Real ROI[16:00] Useless Courses, Forgotten Skills[17:00] Dropping Out and Getting Ahead[18:00] Sales Skills vs. College Classes[19:00] AI and the Future of Professional Work[20:00] Socialization: Real World vs. Campus[21:00] Google Certificates and Online Education[22:00] James Insults His Alma Mater (Again)[23:00] Who Really Wins in the College System?Additional Resources:James Altucher on Twitter: @jaltucherJames’s article archive on college: Altucher Confidential – Why College is a ScamCoursera Professional Certificates (Google, Meta, etc.): coursera.orgKhan Academy (Free Education): khanacademy.orgU.S. Department of Education – College Scorecard: collegescorecard.ed.govTrade School Info & Averages: Trade-Schools.netFederal Reserve Report on Student Loans: federalreserve.govSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:Owning a home has been sold to us as the American dream. But what if it's actually a financial nightmare? In this episode, I talk with my friend Doug Hill about why I think buying a house is a bad idea—not just a little bad, but one of the worst investments you can make. Doug and I disagree on some points, and that's the fun part. This isn't about being contrarian for the sake of it. It's about questioning assumptions that most people never even stop to think about.Episode Description:In this premiere episode of the Crazy Finance series, James Altucher and Doug Hill take on one of the most sacred cows in personal finance: home ownership. James argues that buying a house isn’t the milestone of success it’s made out to be—it’s an expensive, illiquid, and overrated investment. Doug offers a counterpoint rooted in emotional and lifestyle value. Together, they break down the numbers, psychology, and cultural narratives that shape the decision to rent or buy.If you’ve ever wondered whether you should buy a house—or regret that you did—this conversation challenges the conventional wisdom with real numbers and uncommon insight.What You’ll Learn:Why owning a home may be one of the least financially sound decisions you can makeHow homeownership locks you into inflexible geography and limits job mobilityThe hidden costs of maintenance, property taxes, and lost opportunityWhy emotional security often drives people to buy homes, not financial logicHow rental life can be financially and psychologically freeingTimestamped Chapters:[00:00] Homeownership Is a Scam?[01:00] Introducing the Crazy Finance Series[02:00] James’s 11-Item Airbnb Life[03:00] Why Freedom Costs Less Than You Think[04:00] The Myth of "Throwing Away" Rent[06:00] What Makes a House a Bad Investment[07:00] Real Estate vs. Diversified Assets[08:00] The Illusion of Home Equity[09:00] Historical Returns on Housing[10:00] "Found Money" and Forced Savings[11:00] When You Never Truly Own Your Home[13:00] Renting vs. Buying: Lifestyle Tradeoffs[14:00] James vs. Doug: Dominican Property Math[16:00] Renting as Freedom, Not Failure[17:00] The 40-Year Trap of the Down Payment[18:00] Recession Horror Stories[19:00] Emotions vs. Economics[20:00] Getting Stuck (Just Like Factory Towns)[21:00] Why James Still Owns a Home (Kind Of)[22:00] Gender, Culture, and Nesting Instincts[23:00] Listener Homework: Is It Really a Good Investment?Additional Resources:James Altucher on Twitter: @jaltucherU.S. Housing Returns Historical Data: Case-Shiller Home Price Index via FREDMortgage Interest Rates: Bankrate.comU.S. Property Tax Statistics: Tax Foundation – Property Taxes by StateChoose Yourself by James Altucher – AmazonSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:So Chef Curtis Duffy—he’s won Michelin Stars, a James Beard Award. He’s been on Netflix’s Iron Chef, was a judge on Top Chef season 21, and he’s even shown up in The Bear. He runs the Chicago restaurants Ever and Grace, and he wrote this incredible memoir called Fireproof: Memoir of a Chef.I could list all the accolades, but what really got me was his story—it's one of the most intense and heartbreaking I’ve ever read. The kind of story that stops you in your tracks. We talk about all of it—the trauma he lived through, the discipline he built, and what it takes to truly be great at anything. If you're chasing excellence in any part of your life, this episode will hit hard.Episode Description:James sits down with acclaimed chef Curtis Duffy for a raw and powerful conversation that goes far beyond the kitchen. From the trauma of losing both parents in a murder-suicide to earning multiple Michelin stars, Duffy shares the personal and professional disciplines that shaped his life. This isn’t just a story about food—it’s about resilience, focus, and the high cost of mastery. Whether you're building a business, learning a craft, or rebuilding your life, Curtis’s story offers something rare: clarity on what it really takes.What You’ll Learn:The difference between discipline and motivation—and why only one sustains greatness.How Curtis transformed personal tragedy into a lifelong drive for excellence.What separates a 2-star Michelin restaurant from a 3-star—and why consistency matters more than you think.Practical ways to develop expertise, even in everyday tasks (like boiling an egg).The importance of emotional control and quiet leadership in high-pressure environments.Timestamped Chapters:[00:00] Intro: Why Curtis Duffy’s story matters[01:45] Chef vs. metalhead: Black Sabbath and personal intensity[04:50] The family tragedy that shaped everything[10:30] Processing the unimaginable: police, negotiation, and aftermath[13:00] What Curtis wishes he had heard from his mother[15:45] Breaking the cycle of abuse[19:00] Leadership in the kitchen: discipline, not yelling[22:00] Hiring red flags and building the right team[26:00] The value of obsession and sacrifice[30:00] Curtis’s first spark of culinary creativity[32:00] What makes great chefs great[34:00] The science of boiling an egg—and why it matters[36:30] Developing "chunks" of expertise over decades[38:00] Talent vs. skill: what really wins[41:00] The role of discipline and why most people stop short[43:00] Going from chef to restaurateur and media personality[47:30] The pressure of competition shows vs. real kitchens[49:00] How to train consistency into a restaurant culture[52:00] Where restaurants are headed next[53:00] James gets BLT advice from a Michelin-starred chef[56:00] What makes a perfect baguette—and why most are awful[58:00] Final thoughts and how to connect with CurtisAdditional Resources:📖 Fireproof: Memoir of a Chef by Curtis Duffy🍽️ Ever Restaurant – Chicago🍷 Grace (Curtis Duffy’s former restaurant)🥁 Charlie Benante – Drummer for AnthraxOur Sponsors:Elevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audience.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:Miesha Tate—at first, I’ve got to admit, I didn’t know much about UFC or MMA. But Miesha was the World Bantamweight Champion, and she fought Ronda Rousey—probably the most famous female fighter in the sport. I watched one of their fights, and honestly, I don’t know how I’d survive even a quarter of a second.But the conversation we had wasn’t what I expected. Miesha opened up about the mindset behind championship success, the weight of public expectations, and how depression can still hit even after you’ve reached the top. We talked about how personal growth sometimes means burning down everything and rebuilding. This wasn’t just about fighting—it was about resilience, reinvention, and figuring out what matters when the title belt doesn’t solve your problems.It was raw, honest, and eye-opening. I look forward to talking with her again.Episode Description:What happens when you reach the top of your field—and it still doesn’t fix what’s broken inside?Former UFC Bantamweight Champion Miesha Tate shares the brutal truth about chasing success, surviving toxic relationships, and rebuilding her life from rock bottom. In this candid conversation, Miesha and James explore the psychology of high performance, the danger of tying self-worth to achievement, and how to know when it's time to walk away—even from something you love.She tells stories from her early wrestling days to her UFC career, opens up about depression, and explains why learning to fail—and rebuilding—might be the most important skill of all.What You’ll Learn:Why reaching your ultimate goal might make you feel worse, not betterThe hidden costs of high achievement and fameHow to identify toxic environments and take back controlWhy learning to “rebuild your metaphorical home” is essential to resilienceHow Miesha used mindset—not just physical training—to fight through adversityTimestamped Chapters:[00:00] The Broken Nose That Started It All[03:00] High School Wrestling with the Boys[06:00] Early Lessons in Grit and Gender Barriers[08:00] From Wrestling to MMA: Embracing the Unknown[11:00] Chasing the Win, Fearing the Loss[13:00] Building the Metaphorical Home[17:00] Blood, Grit, and the First Amateur Fight[21:00] Getting Knocked Out and Coming Back[27:00] The Problem with Thinking Winning Will Save You[34:00] Fighting Ronda Rousey: Lessons in Obsession[39:00] Training for the Unexpected[45:00] When Success Doesn’t Fix Anything[50:00] Rock Bottom and a 10-Day Drive to Nowhere[55:00] Rebuilding from Scratch[59:00] Miesha’s Life Today: Mindset, Family, and HomesteadingAdditional Resources:Miesha Tate on InstagramMiesha Tate’s Podcast: Built for GrowthUFC Fighter Profile: Miesha Tate“The Weight of Gold” HBO DocumentaryOur Sponsors:Elevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audience.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:One of the funniest guys I’ve ever spoken to—Dave Barry. I always love talking to him. He’s been America’s top humorist since the early ’80s with a syndicated column in 500 newspapers and a long list of bestselling books. This is his third time on the podcast, and his latest book, Class Clown: Memoirs of a Professional Wiseass, is out now.We get into everything—his process, his adventures, and his signature style of humor that’s made him a legend. It’s always fun with Dave.Episode Description:James sits down with Dave Barry to explore the surprising journey behind his new memoir, Class Clown. Dave shares how his humor evolved from playful everyman columns to a more personal, story-driven style. They talk about his outrageous adventures, from picking up his son in the Oscar Mayer Wienermobile to getting booed by telemarketers and dedicating a sewage station in his honor. They also break down the shifting landscape of writing, how syndication shaped Dave’s career, and why modern humor feels trapped in political silos.This is a rare chance to hear how one of America’s greatest humorists built a career by doing things to write about them—and why his readers became his closest allies.What You’ll Learn:Why Dave Barry was initially reluctant to write a memoir.How performing outrageous stunts became central to his writing.The critical role of reader engagement in building the success of his humor column.How the writing industry—and the path to building an audience—has radically changed.Dave’s candid perspective on modern political humor and why neutrality feels impossible today.Timestamped Chapters:[00:00] Introduction to Dave Barry[01:00] Writing a Memoir: The Journey Begins[02:00] The Humorist’s Approach: Balancing Persona and Reality[03:00] Adventures in Journalism: Creating Stories by Living Them[05:00] Tactical Humor: Rivalries, Stunts, and Getting Involved[08:00] When Humor Becomes the Story: Telemarketers and Public Reaction[12:00] Building a Community: How Dave Engaged His Readers[17:00] The Syndication Era: How Writing Used to Pay[23:00] The New Writing Economy: Substack and the Digital Shift[28:00] Assault Humor and the Loss of Neutral Comedy[31:00] What’s Next: Substack, Slowing Down, and Florida’s Wild Identity[35:00] Writing Novels vs. Columns: Dave’s Fast-Paced Storytelling Style[41:00] Stand-Up Comedy and the Influence of Nate Bargatze[44:00] Comedy Club Lessons: James on Bombing and Recovery[46:00] Criticism: Dave’s Approach to Bad Reviews[47:00] Farewell: Dave’s Thoughts on Humor, Writing, and LegacyAdditional Resources:📖 Class Clown: Memoirs of a Professional Wiseass by Dave Barry📖 The Kite Runner by Khaled Hosseini🎤 Nate Bargatze Official Website🎤 Jim Gaffigan Official Website🎤 Hunter S. Thompson’s Fear and Loathing on the Campaign Trail ’72🎤 P.J. O'Rourke’s Official Website (archived)See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Notes from James:I had no idea this conversation would go where it did. I thought we’d talk chess. Instead, we talked about life, trauma, manipulation, redemption… and how one of the world’s most popular games can be both a tormentor and a savior.Episode Description:In this raw and powerful episode, I sat down with Danny Rensch—International Master, Chief Chess Officer of Chess.com, and author of the upcoming memoir Dark Squares—to uncover a story that’s anything but a typical chess tale. Raised in a spiritual cult obsessed with chess, Danny’s path to mastery involved trauma, isolation, and resilience. We go deep into the psychological aftermath of cult life, the beauty and torment of the game that saved him, and how he helped turn Chess.com into a global phenomenon with over 200 million users.This isn’t just an episode about chess. It’s about survival, identity, and how to turn pain into purpose.What You’ll Learn:How Danny’s obsession with chess began inside a controlling cultThe complicated relationship between talent, trauma, and identityHow being taken from his family at age 12 shaped his worldviewHow Chess.com exploded from 100k subscribers to millions after The Queen’s GambitWhy cheating in chess is a growing threat—and how they’re fighting itWhat the Hans Niemann scandal revealed about the future of the gameHow to build resilience and purpose from even the darkest beginningsTimestamps:00:00 Introduction: A Unique Upbringing and Chess Obsession00:43 The James Altucher Show: Welcoming Danny Wrench00:58 Danny Wrench's Journey: From Chess Prodigy to Business Success03:19 The Dark Side of Chess: Cult Life and Personal Struggles12:38 Chess.com: Growth and Success14:34 The Impact of COVID-19 and The Queen's Gambit20:30 Cheating Scandals and Controversies in Chess26:26 Future of Chess: Technology and Cheating31:14 Conclusion: Living the DreamOur Sponsors:Pack up and go even further with the Defender 110. Learn more at LandRoverUSA.com/DefenderHead to rugiet.com/JAMES and use code JAMES to get 15% off today!Secure your online data TODAY by visiting ExpressVPN.com/ALTUCHERSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:Man, what a fascinating career Robert Rosenkranz has had—multi-billionaire, involved in virtually every part of finance and American industry. He wrote a book called The Stoic Capitalist, and what really stands out is how he's actively applied stoic principles to achieve immense success throughout his career. Even from a young age, stoicism played a crucial role, guiding him through critical business decisions. It's a real pleasure speaking with Robert—an American icon.Episode Description:James welcomes Robert Rosenkranz, author of The Stoic Capitalist: Advice for the Exceptionally Ambitious, to discuss how applying stoicism's timeless principles helped him navigate pivotal career decisions and financial challenges. Robert candidly shares his experiences—from early high-stress deals to launching a private equity firm where he risked his entire net worth—and explains why stoic philosophy remains essential for rational decision-making in business and life. The conversation highlights how embracing uncertainty and questioning assumptions can lead to clarity and resilience in a constantly changing world.What You'll Learn:How to differentiate between rational risks and emotional fears in critical decisions.Strategies for recognizing and overcoming cognitive distortions like catastrophizing.Practical applications of stoicism in modern investing and entrepreneurship.Insights into adapting to rapid technological changes, particularly AI.The importance of spousal support and personal relationships in career success.Timestamped Chapters:[00:00] Introduction to Robert Rosenkranz[02:00] The First Major Deal and Stoic Principles[05:00] Risk and Rational Decision Making[09:00] The Role of Biographies and Early Influences[12:00] The Importance of Spousal Support[28:00] Stoicism and Cognitive Behavioral Therapy[34:00] Exploring Financial Trends and Technology[35:00] The Impact of Artificial Intelligence[36:00] Addressing Fears and Job Displacement[37:00] Adapting to Technological Change[44:00] The State of the US Economy[48:00] Investment Strategies and Market Behavior[54:00] Stoicism and Its Influence on Investing[57:00] The Role of Social Media in Society[63:00] Reflections on Public Service and Education[67:00] Conclusion and Final ThoughtsAdditional Resources:The Stoic Capitalist by Robert RosenkranzHow to Think Like a Roman Emperor by Donald RobertsonThe Obstacle Is the Way by Ryan Holiday"The Smoot-Hawley Tariff and the Great Depression" - The EconomistOpen to DebateOur Sponsors:Pack up and go even further with the Defender 110. Learn more at LandRoverUSA.com/DefenderHead to rugiet.com/JAMES and use code JAMES to get 15% off today!Secure your online data TODAY by visiting ExpressVPN.com/ALTUCHERSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Notes from James:When I turned 40, I was depressed. I checked the top 50 chess players and saw only one person around my age: Viswanathan Anand. That moment gave me hope.Episode Description:I met one of my lifelong heroes—five-time World Chess Champion Viswanathan Anand—and got to sit down with him at the Norway Summit to unpack what it really takes to stay at the top… for four decades. We didn’t just talk about chess—we talked about life, legacy, improvement, and how to overcome self-doubt at any age.Vishy and I broke down how talent evolves, why confidence matters more than skill early on, and how he battled through plateaus, age, and even failure to remain among the world’s elite players—well into his 50s. This episode is a masterclass in longevity, performance, and reinvention.Whether you're into chess or not, Vishy's insights apply to anyone striving to master their craft, overcome obstacles, and stay in the game.What You’ll Learn:The real reason most people plateau—and how to push through itWhy youth is powered by “inaccurate self-confidence” (and why that’s not a bad thing)How to adapt when the game—or the world—changes faster than you can keep upWhat to do when your best effort still leads to lossHow to retrain your mindset after failure or self-doubtWhy reinvention is a lifelong skill, not a one-time fixTimestamps:00:00 The Relentless Nature of Chess00:39 Meeting My Hero: Viswanathan Anand01:12 A Personal Story of Inspiration02:55 Interview with Viswanathan Anand06:43 The Evolution of Chess and Personal Growth28:57 The Role of Youth and Confidence in Chess31:14 Concluding Thoughts and Future ProspectsSponsors:Visit “LandRoverUSA.com” to learn more about the Defender one-tenTo get 6 bottles of wine for $39.99, head to NakedWines.com/JAMES and use code JAMES for both the CODE AND PASSWORD.Elevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audience.Visit northwestregisteredagent.com/james and start building something amazing! Get more with Northwest Registered Agent at northwestregisteredagent.com/james.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:So I’ve been doing this podcast for a long time—over 1500 episodes—and I’ve spoken to everyone from billionaires to best-selling authors, athletes to entrepreneurs. But there are a handful of episodes that still ring in my ears years later. One of them was Episode 156 with Gary Vaynerchuk.I was just re-listening to it while pulling together notes for a potential book, and I realized this conversation is timeless. It’s not about hype. It’s about freedom. Gary’s blueprint—learn, build, create community, stay self-aware—is the real deal. No shortcuts. No tricks. Just pure, actionable wisdom. Whether you’re 23 or 53, if you're serious about building the life you want, this one’s worth a listen.Send it to your kids. Your friends. Your future self.Thanks again for listening.Episode Description:In this re-release of one of the most downloaded episodes of The James Altucher Show, James sits down with Gary Vaynerchuk just before the release of his book #AskGaryVee. What unfolds is a candid, highly tactical conversation about business, content creation, self-awareness, and the true meaning of entrepreneurship.Gary breaks down his framework for success—from selling wine via YouTube in the early 2000s to launching VaynerMedia and investing in Facebook, Twitter, and Tumblr. He also explains why patience, practicality, and micro-failure are essential ingredients for long-term freedom.This isn’t motivational fluff. It’s the strategy, mindset, and playbook of someone who’s been in the trenches—and is still hungry.What You’ll Learn:Why "entrepreneurship" is really just a path to freedom—not fast cashHow Gary made (and learned from) multiple startup failures in 2009Why content marketing is about sincerity, not SEO hacksHow to test new business ideas through arbitrage—like flipping Jets gear on AmazonA tactical breakdown of self-awareness (and how to get it from people you trust)Timestamped Chapters:[00:00] Leisure vs. Freedom: What You’re Really Trading[01:00] Recommending Competitors as a Sales Tactic[03:00] Early YouTube, Wine Library, and ROI Before Social Was “Social”[06:00] Entrepreneurship vs. Lifestyle Marketing[08:00] Ego, Confidence, and What Scares Gary Vee[10:00] The Trainwreck Year: 2009 and Four Failed Startups[12:00] Experiments, Micro-Failures, and Million-Dollar Misses[14:00] Offense vs. Defense in Business[15:00] Building Trust Through Sincerity in Content[18:00] Self-Awareness: Gary’s Most Important Entrepreneurial Trait[22:00] The Real Numbers: What It Means to Be in the 1%[25:00] Leisure Costs More Than You Think[29:00] Why Gary Loves Losing and Chasing More Than Winning[34:00] The Self-Awareness Dinner Party Hack[38:00] Redefining Success: From $213K to $87K and Happy[42:00] Clouds and Dirt: Finding Your North Star and Executing in the Weeds[43:00] The Arbitrage Blueprint: eBay to Amazon[47:00] Community Building Through Twitter and Micro-Engagement[49:00] Jab, Jab, Jab, Right Hook (And What People Get Wrong About It)[52:00] Avoiding Negative Energy in Business and Relationships[54:00] Tactical Social Media Growth: Commenting, Listening, Engaging[56:00] Scaling Beyond Arbitrage: Events, Podcasts, ProductsAdditional Resources:#AskGaryVee: One Entrepreneur's Take on Leadership, Social Media, and Self-Awareness (Amazon)Gary Vaynerchuk’s TwitterWine Library TV ArchivesVaynerMediaDailyVee on YouTubeOur Sponsors:Pack up and go even further with the Defender 110. Learn more at LandRoverUSA.com/DefenderElevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audienceTo get 6 bottles of wine for $39.99, head to NakedWines.com/JAMES and use code JAMES for both the code AND PASSWORDDon’t wait, protect your privacy, build your brand and set up your business in just 10 clicks in 10 minutes! Visit northwestregisteredagent.com/james and start building something amazing!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:So the question is, I really feel that in order to get not good at something, but great at something, you have to be obsessed. You can't just wake up and decide to be obsessed—it has to be deep, almost irrational. Obsession is like addiction. It throws your life off balance, and yet... there’s this insane joy when you enter the subculture of your obsession and get better at it.I’ve seen this recently in crypto. I saw it in chess in Norway, commenting on what might’ve been the best chess tournament ever. And I felt it again when I sat down with Dirk Jan ten Geuzendam from New In Chess.We didn’t just talk about chess. We talked about obsession, aging, failing at something you love, and trying to find your place in a subculture that’s moved on without you.If you care about learning, obsession, or just love chess, you’re going to get something out of this episode. Dirk and I recorded this in Stavanger, Norway. I hope you love this conversation as much as I did being a part of it.Episode Description:What does it mean to return to your first love after nearly 30 years away? In this special crossover episode, James Altucher sits down with Dirk Jan ten Geuzendam, editor of New In Chess magazine, to reflect on his lifelong (and recently rekindled) obsession with chess. They explore how obsession shapes mastery, why wisdom sometimes trumps raw skill, and what it’s like to try and reclaim an old identity as an older version of yourself.James opens up about losing games to kids half his age, obsessively chasing improvement, and why it still might be okay to fail—as long as the journey is honest. From teenage blitz tournaments to dinner with Garry Kasparov, from neuroscience to narrative writing, this episode is as much about how to live as it is about how to play.What You’ll Learn:Why obsession is both a superpower and a dangerHow James approaches relearning chess after a 27-year breakWhat changes in the brain as we age—and how to work with itThe surprising ways chess opens doors in life, business, and writingWhy storytelling and vulnerability matter more than "success" aloneTimestamped Chapters:[00:00] The Power of Obsession[01:00] Travel Tales: Norway and Crypto[03:00] Chess Commentary and Podcasting with Dirk Jan[05:00] Dirk Jan's Intro on James Altucher[08:00] James' Curiosity and Love of Learning[10:00] Starting Chess at 17 and Becoming Addicted[13:00] Losing to Irena Krush and Facing Limits[17:00] Chess, Ego, and Real-World Consequences[22:00] How Chess Skills Apply to Business Problems[26:00] Writing as a Path Through Vulnerability[33:00] Returning to Chess: Memory, Aging, and Rediscovery[37:00] Eric Rosen, Coaches, and Mental Decline[41:00] Pattern Recognition vs. Calculation[47:00] What Makes Chess Players Unique[50:00] Interviewing Kasparov, Judit Polgar, Hikaru[56:00] Obsession and the Myth of Talent[58:00] Will the Book Get Written?[60:00] The James Altucher Invitational[62:00] Reflecting on the JourneyAdditional Resources:📘 New In Chess Magazine – The legendary publication covering elite and amateur chess alike🎙️ New In Chess Podcast – Hosted by Dirk Jan ten Geuzendam📚 Choose Yourself by James Altucher📺 Eric Rosen’s YouTube Channel – Where James first relearned modern chess💻 Chess.com – Popular online chess platform♟️ lichess.org – Free, open-source chess platform📘 Game Changer by Matthew Sadler & Natasha Regan – On AlphaZero’s influence on modern chess🧠 Andrew Huberman's Podcast – Neuroscience insights referenced in the episodeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:Michael Dell. Founder of Dell. I remember in college, hearing about this kid who was building computers in his dorm and making millions. I thought it was a myth. It wasn’t. He’s the real thing—and he just kept going.I wanted to understand what drove him, what it felt like to deal with Carl Icahn trying to wrestle his company from him, and what success feels like after decades of being in the game. Also: I had to ask why Dell didn’t invent Google. That, plus how he’s now thinking about AI, cancer, and what “focus” really means.Episode Description:James Altucher sits down with Michael Dell, founder and CEO of Dell Technologies, to trace the entire arc of Dell's career—from building computers in a college dorm room to defending his company against Carl Icahn and taking it private. In this candid conversation, Dell shares how early obsession with tech and business turned into a multibillion-dollar global enterprise, the lessons he’s learned about leadership, and how he’s positioning for the future with AI, cybersecurity, and gene tech on the horizon.This is more than a business story. It’s about risk, conviction, reinvention—and knowing when to walk away from Steve Jobs.What You’ll Learn:How Dell’s dorm-room business scaled to $80,000/month before he even left collegeWhat Michael Dell really thought during his showdown with Carl IcahnWhy most big companies fail to innovate—and how to keep a startup mindsetHow Dell Technologies is preparing for the explosion in AI and edge computingWhat makes a good leader at the head of a $100 billion companyTimestamped Chapters:[00:00] James introduces Michael Dell and the origin story of Dell Computers[01:00] The economics of building PCs in the early 1980s[03:00] Winning state bids with a bike and a dorm room[05:00] Pressure to become a doctor—and the 10-day “intervention”[10:00] Meeting Steve Jobs and licensing DOS from Bill Gates[13:00] Dell’s early B2B focus and international expansion[15:00] Going public and the Icahn showdown[18:00] How activist investors play poker with billion-dollar stakes[21:00] What focus really means in business[24:00] Defining leadership at global scale[26:00] Encouraging innovation inside massive companies[28:00] The failed Mac OS licensing deal[30:00] Philanthropy, education, and urban poverty[33:00] COVID lockdowns and a $100M response[35:00] The future of work and city migration[39:00] AI, edge computing, and exponential data[42:00] Gene editing, mRNA vaccines, and solving cancer[45:00] Blockchain in enterprise (no bitcoin on Dell’s balance sheet—yet)[47:00] Why cybersecurity is an arms race\Additional Resources:Play Nice But Win – Michael Dell’s memoir (Amazon)Dell Technologies – Official websiteJudge rejects Icahn's move on Dell buyout – CT InsiderRichard Florida on the future of cities – Vital City NYC interviewWhat is CRISPR? – Broad InstituteHistory of MS‑DOS – WikipediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.